In Boston, urban trail building and hiking are traditions that date back to the late 19th Century, when the city hired Frederick Law Olmsted to restore the current of the Muddy River and create a network of linear parks and green spaces that bridged neighborhoods. This game-changing parks system, the Emerald Necklace, was arguably the first urban trail in Boston. Since then, several more trails have taken shape, to the point where Outside magazine named the City of Boston one of America’s top hiking destinations!
The creation and development of the Walking City Trail is a continuation of this civic tradition. We highly recommend checking out all of Boston’s beautiful urban trails, which we’ve compiled on this page.
ThE EMERALD NECKLACE
Olmsted’s baby (which he moved to Boston to work on), the Emerald Necklace is a linear parks system—an interconnected chain of green spaces like Boston Common, the Fenway, Arnold Arboretum, and Franklin Park, draped across multiple neighborhoods. You can hike from one end of the Necklace to the other in 7-9 miles, depending on which park paths you decide to explore, and the Emerald Necklace Conservancy organizes special events in the parks during summer.
THE FREEDOM TRAIL
Arguably Boston’s most famous urban trail, the Freedom Trail runs 2.5 miles across Downtown, the North End, and Charlestown, from Boston Common to Bunker Hill Monument. Marked by a solid line of red bricks installed in sidewalks and streets, the Freedom Trail visits 17 places that were crucial to the founding of the United States and the beginning of the Revolutionary War. Guided and self-guided tours of the trail are offered throughout the year.
THE BLACK HERITAGE TRAIL
Winding 1.6 miles through Beacon Hill and managed by the National Park Service, Boston’s Black Heritage Trail visits important historic sites in the neighborhood that was home to the city’s largest pre-Civil War African-American community. The trail features public artwork like the 54th Regiment Memorial and it concludes at the Museum of African-American History. You can take a self-guided tour of the Black Heritage Trail by downloading the free NPS app.
THE BOSTON WOMEN’S HERITAGE TRAIL
Created in the late 1980s by a coalition of Boston teachers, librarians, and students, the Boston Women’s Heritage Trail is a collection of curated walking routes through neighborhoods such as Back Bay, Roxbury, East Boston, and Chinatown—all rooted in chapters of city history in which Boston-based women broke ground and changed the status quo. Self-guided tours are available through the trail website, and private in-person tours can be commissioned as well.
THE IRISH HERITAGE TRAIL
Immigrants have long played an essential role in the development and flourishing of Boston. The Irish Heritage Trail offers a window into the growth of the city’s Irish American community. The trail extends beyond the City of Boston, visiting towns like Hull and New Bedford. The Boston segment includes a curated walk in Downtown Crossing featuring landmarks such as the Boston Massacre Memorial and the Boston Public Library. Free maps are available at the trail website.
THE WALK TO THE SEA
The Norman B. Leventhal Map & Education Center is a Boston-based wayfinding institution and the creator of the Walk To The Sea trail. This 1-mile interpretive walking route begins at the Massachusetts State House in Beacon Hill and leads to the seabreezy docks of Long Wharf, where visitors can gaze across Boston Harbor. Trail markers are installed along the route and additional navigational resources are available for free on the trail website.
THE BOSTON HARBORWALK
The shoreline of Boston Harbor meanders from the Neponset River in Mattapan to Belle Isle Marsh in East Boston, the Boston Harborwalk is a 43-mile trail that allows you to walk the coast! The route includes beaches, parks, wetlands, business districts, and industrial areas. It’s almost contiguous, which means that there are a gaps where there’s no designated pathway. (But in 2022, one of us found a way to thru-hike the entire thing.) Maps are available on the trail website.
THE ART WALK PROJECT
Artists imbue the cityscape with texture, color, and the elements of surprise, and in 2020, during the first round of Covid-19 lockdowns, Boston-based multimedia artist Julia Swanson created a series of walking routes that “explore creativity and community through public art.” The Art Walk Project walking routes spotlight Boston neighborhoods such as Allston-Brighton, South Boston, and the Kendall Square area in nearby Cambridge. Free maps are available.
THE SOUTH BAY HARBOR TRAIL
Highways have long divided cities, sequestering communities from opportunity. The South Bay Harbor Trail tackles this structural issue by offering a walkable, bikeable passage beneath I-93 from Ruggles Station in Roxbury to the Fort Point Channel area of the Seaport. The trail is a joint venture between Save The Harbor/Save The Bay and the City of Boston. While the trail is still under construction, the route can be walked today. A free map is available on the trail website.
THE BOSTON GREENBELT TRAIL
What if you could hike 90 miles around Boston, from the North Shore to the South Shore, through forests, bogs, and town centers? David Loutzenheiser, a transportation planner with Boston’s Metropolitan Area Planning Council, has discovered a way to do this. The name of this epic route is the Boston Greenbelt Trail, and while it’s a proposed trail for now, almost all of the route exists and is walkable. A working map of the trail is available here. (Look for a line of red dashes going south from Marblehead by Pickering Point, to Nut Island in Quincy.)